Ask HN: Career Advice – Management Regrets and IC Life

Hi HN, Since none of my social circle is in tech - I though I'd ask HN regarding my career situation. I've two different pathway and I'm struggling to decide. 0) Director position (for AI) within company, ~700 employees (current) This company is not an engineering or AI company. Tbh, I'm not simulated by the problem space my work is in. It's comfy - I like my colleague and my team. Too much bureaucracy coming from startup world. Quality of engineering is OK - I guess stack and team is a bit less mature. I also feel like I will not be technically up to date in AI world as I used to be as a lead. I feel like this would really tie me to data science specialty for later career, which I don't want to do. What would be lateral path from this position? I can think of Engineering Manager or VP/Dir of Engineering - but I would always lose out to peers due to AI heavy work history. 1) Tech Lead/Sr. Software Eng within startup , <70 employees (startup is growing) This company is an engineering company, where software engineering tools are sold as SaaS. It's all new technology stack - and problem space (language analyses) are challenging and very interesting. But my title would drop a quite a bit - all my non tech friends recommended not to take this position. This position is remote - but have to be in US. I feel like this would provide me lot more optionality and new learning opportunity. I'm really excited about this (maybe this is the novelty chasing brain of mine). Both are in US - both are paying roughly the same in base, but startup significantly more in stocks. I don't have any dependents. Any practical/Machiavellian advice? Any stories of regretting going further in mgmt position or getting tied into specialty?